For Max Poglia, simply being in Florence can be overwhelming. “There are so many beautiful things around you, you almost have a breakdown,” says the Brooklyn-based designer of handcrafted knives and bags. Of course, the city’s art and architecture have been making visitors lose their grip for centuries. But Poglia is no ordinary tourist. He’s visited Florence a few times as a vendor at Pitti Uomo, the exclusive menswear event that has turned this otherwise changeless (some might say stubbornly trend-resistant) city into an increasingly important hub for a new generation of global style trendsetters.

Twice a year, these canny enthusiasts descend on Florence to make deals and soak up old-world inspiration for both their own work and legions of Instagram followers. “You find some of the best-dressed men on the planet,” says Scott Schuman, a.k.a. The Sartorialist, who has been photographing said men against Florentine backdrops of peeling frescoes and marble piazzas for nearly a decade. “What those visuals mean to young guys all over the world is pretty staggering. There are people imitating Pitti street style in Cape Town.”

Santa Maria del Fiore (The Duomo) obviously makes for a handsome backdrop. But for Poglia and other nostalgia-minded Brooklyn innovators, Florence appeals more as an unself-conscious embodiment of craft and slow-made authenticity—evident in everything from leather goods to wine and tailoring. “What feels like a movement in New York, in Florence just is,” says Andrew Livingston, a friend of Poglia’s and the co-founder of Queens-based fashion brand Knickerbocker Mfg. For the classics-seeking new guard, novelty and cutting-edge design are not the point. “All of us gravitate to the same places in Florence,” says Ouigi Theodore, owner of the vintage-inspired clothier Brooklyn Circus. “The ones that have comfort, character, personality, and S-O-U-L.”

Poglia first got to know Theodore and Livingston in New York, although regular Florence meet-ups (all three attend Pitti as wholesale vendors) have brought them even closer. Poglia, originally from Brazil, has found a mentor of sorts in Milan-based designer Alessandro Squarzi, who also happens to be one of Schuman’s top photo subjects, and this multi-generational quartet often canvas the city together after the shows. “I think what’s interesting right now is that we’re all referencing the past in our work, which makes the young guy just as interesting as the old guy,” Theodore says. (To say nothing of the young woman: Grandpa Style blogger Ashley Owens, known for her ability to pull off a men’s suit, sometimes joins Poglia’s crew during Pitti.)

Poglia, who speaks fluent Italian, loves popping into no-name leather workshops unannounced. At one, he remembers asking if he could buy a gold-leafed case, which the shop’s artisans had made using a traditional technique. The owner declined to sell but invited him in for a look around—and then, as Poglia was leaving, offered him the case as a gift. “That’s what Florence is all about. Every time I go, it’s something magical,” the designer says. “People complain about the tourists, but they don’t bother me. I just get busy trying to find my favorite things.”

Where the Boys Are

From a 130-year-old snack shop to the best of men’s vintage, this group of friends’ favorite addresses have seriously stood the test of time.

The Scene-Making Lunch Spot

Seasoned waiters in bow ties and white shirts work the room at Cammillo. “Great cuisine and a ’20s Al Capone vibe,” enthuses Alessandro Squarzi of this family-run trattoria. Scott Schuman, who touts the open kitchen and informal atmosphere, has hosted the likes of Kanye West and John Malkovich at private lunches and dinners here during Pitti. Max Poglia recommends the fritto misto and fiore di zucca.

For an Authentic, Tourist-Free Dinner

Squarzi routinely takes the Americans to Alla Vecchia Bettola, a 37-year-old osteria near the Torrigiani Garden, for simple Tuscan fare. (It’s across the Arno, about a 15-minute cab ride from the city center.) “They’re famous for their meat, but the crostini and pastas are also really great,” Squarzi says. “And I love that they still make espresso with the moka pot, not the new coffee machines.”

Procacci, a 130-year-old gourmet grocery, specializes in the diminutive truffle-paste sandwich called a panino tartufato. “It’s just a snack,” Poglia says—but with a glass of prosecco, it’s a distinctively Florentine one. Vintages by Antinori, the fourteenth-century winemaker responsible for the Super Tuscan movement, are served in a recently renovated space with painted wood and antiqued steel.

Unique fabrics and French and Italian vintage pieces are among the prime goods at Ceri Vintage, where owner Danilo Ceri keeps a sewing machine in the back. Andrew Livingston praises the “sick trousers”—many made of moleskin, a heavy cotton—and no-nonsense miners’ jackets. “He has a really good eye for things from the ’50s and beyond,” notes Ouigi Theodore, who once found himself fighting here with Poglia over a prize union suit.

The Retro-Fashion Mecca

Curator Carlo Andreani’s expert mixing of sportswear and designer labels, men’s and women’s, makes Desii Vintage one of the city’s top stops. Think Louis Vuitton and Chanel handbags, tweed caps, and Adidas Originals. “It’s crazy how affordable some of the European workwear is,” Livingston says, and the collection of fedoras is top-notch.

Dig for Rare Treasures

Treasure hunting at the flea market at Piazza Santo Spirito (on the second Sunday of every month) has gotten harder as more vintage and antiques connoisseurs have started picking over the city’s riches. Still, it delivers. “There’s a lot of great old books,” notes Livingston, who recently came upon a gold-foil cover design here that inspired a Knickerbocker garment box.

Save Time in a Bottle—Literally

Launched some 400 years ago, Officina Profumo-Farmaceutica di Santa Maria Novella, the high-end Florentine perfumer and apothecary, is one of the oldest lifestyle brands on the planet. (Its popular rosewater was used as a Black Plague disinfectant.) The palatial trappings, in addition to the fine swirl of herbal/floral scents, make the flagship store a must-visit. “It’s the perfect place to get presents,” notes Schuman, who leaves many of his own Santa Maria Novella soaps and lotions unopened. “No one does packaging like them. Sometimes I buy just for that.”

A remarkable joint effort between Florentine leather-business families and Franciscan friars, who converted the old dormitory wing of a thirteenth-century church, the Scuola del Cuoio manufactory and crafts school has trained disadvantaged city residents to become skilled artisans since the end of World War II. The best students are hired to stitch together the stylish items (wallets, belts, and desk accessories, done in materials ranging from calfskin to alligator) sold at the on-site store.

The Best All-Day Hangout

Occupying a prime location on the Piazza della Repubblica for about a century, Caffè Gilli is a popular meeting place during the shows. “We start the day with breakfast here—cappuccino and croissants—or end it with late-night drinks,” Poglia says.

For a Flawless Negroni

More of a hot spot in the summer, Harry’s Bar, a classic haunt along the Arno, originally opened in 1953 and maintains much of its mid-century charm, from the Murano glass lamps to the demure martini glasses. “It’s a favorite spot for a proper Negroni,” Poglia says (the cocktail was invented in Florence). The Bellini is another go-to.

Where the Well-Heeled Fashion Set Stays

Fresh flowers, wingback chairs, zebra prints, cashmere throws, and fine etchings packed salon-style onto the walls are among the stylish touches at J.K. Place Firenze, a 20-room hotel in the centro storico. “I love every little detail,” says Squarzi, who stays here whenever he’s in Florence. And its lounge bar is one of the swankest spots in town for a nightcap.